About the job
MissFit Coaching · Remote (Global) · HQ in Chicago USA - Global Team - Contract - Full-time Reports to: Founder & CEO · Direct reports: None — this role operates through influence and documentation, not managerial authority
About MissFit Coaching
MissFit Coaching is an executive career-coaching and reverse-recruiting practice — in plain terms, we help executives run their job search like a business — serving mid-career, white-collar professionals in job transition. We run a fast-moving, distributed team and hold ourselves to the same standard of precision and follow-through we ask our clients to bring to their own job search.
About the Role
We're hiring a Director of Operations to be the connective tissue across our Engineering, Client Services, and Operations functions — and to own product management for our internal client-delivery platform, which we build and run like a real software product, not a side project. This is a senior operating role, not an entry point into operations — you will be trusted with cross-functional governance and product decisions from day one, reporting directly to the Founder & CEO.
This is not a hands-on delivery role — our Client Services team handles client work directly, and our development partners write the code. What this role owns is the operating rhythm and the product itself: plans get built, work gets tracked, status gets reported honestly and on time, the roadmap reflects what the business and its users actually need next, and nothing depends on someone chasing it down.
Be clear-eyed about what makes this role hard: you will be accountable for other people's deliverables — engineering output, client-services follow-through, a peer's task list — without having formal authority to manage them. You will hold named colleagues to a standard through relationship, documentation, and persistence, not through org-chart power. On the product side, you will be the single owner of the relationship and roadmap across both of our technical partners — our external development team and our AI automation partner — which means reconciling two different workstreams into one coherent product direction instead of just relaying requests to whichever one is easiest to reach. This is the hardest part of the job, and it is the part we are hiring for most deliberately. If "governance without authority" sounds abstract, picture this: a colleague tells you something is done, and it's your job to verify that before you report it upward — even when that's uncomfortable.
You'll be the single point of accountability for whether the business has a clear, current, and truthful picture of what's happening across the team every week — and for whether the platform we run our business on is actually getting better, not just getting built.
One more thing, stated plainly: you will not be chased. You are the chaser. No one — including the Founder & CEO — should ever need to follow up with you to find out where something stands. If a report is late, a blocker is stuck, or a colleague has gone quiet, you surface it before anyone has to ask. That direction only runs one way in this role.
Operations & Governance
- Cross-functional governance across Engineering, Client Services, and Operations — keeping all three coordinated against one shared plan.
- The 90-Day Working Plan ("30-60-90") — building it, keeping it current, and reporting against it every week.
- ClickUp as the single system of record for all non-client-delivery work: loading approved action items, assigning owners and due dates, and keeping the board accurate and current.
- Weekly leadership reporting — consolidating status across every department into one clear, specific report, delivered on schedule without being asked.
- Rollout and adoption of operating standards (for example, our daily commit/close tracking system for Client Services) — not just announcing a new standard, but staying with it until the whole team is actually using it.
- Proactive status reporting on any major initiative you're driving — leadership should never have to ask where something stands.
Product Management for the MissFit Platform
- Roadmap and prioritization — deciding, with the Founder & CEO, what gets built next by weighing client and Client Services feedback against engineering capacity and business priority. You own the sequencing, not just the task list.
- The user feedback loop — systematically collecting input from clients and the internal team actually using the platform, and turning it into prioritized, well-defined requirements instead of ad hoc requests.
- Feature specs and QA ownership — writing complete requirements documents (PRDs), and verifying shipped features actually work as intended, with real users, before they reach clients or staff. Shipped is not the same as done; done means verified.
- Product metrics — defining and tracking how the platform is actually performing: feature adoption, staff usage rates, client engagement, and any measure that tells you whether the product is improving the business, not just accumulating features.
- Single ownership of both technical relationships — you are the one person who owns the roadmap and requirements conversation across our external development team and our AI automation partner, reconciling their work into one coherent product direction.
What We're Looking For
- Proven experience in operations, project management, or program management — ideally in a small, fast-moving company where you owned process across multiple functions at once.
- A track record of building and running structured reporting cadences (weekly reports, project trackers, status dashboards) that leadership actually relies on.
- Comfort working directly with a founder/CEO and communicating in specific, factual, no-filler language — we value clarity over polish.
- Direct experience owning a product roadmap and writing requirements documents for a software product, even a small or internal one — you don't need to write code, but you need to have made real build-vs-defer decisions and lived with the results.
- Experience running a user feedback loop — turning scattered input from end users into prioritized, specific requirements, not just a backlog of requests.
- Experience managing multiple technical or development partners at once, reconciling their work into a single coherent direction rather than treating each as a separate, disconnected workstream.
- Strong written communication in English, since most of our coordination happens asynchronously in writing (email, Slack, shared documents).
- Self-directed follow-through — you flag blockers before you're asked, and you don't wait for a reminder to deliver something you already committed to.
- A demonstrated habit of verifying status before reporting it — you check that a task is actually done before you tell leadership it's done, even when the person who told you otherwise is a colleague you like and trust.
- Comfortable holding peers and vendors accountable to deadlines without having formal authority over them.
Work Style and Logistics
- Location: Fully remote. Open to candidates in any country.
- Schedule: We generally align to USA hours - 7 a.m. or so to about 4 p.m. or so. Check what that means in your local time zone before applying — for many non-U.S. time zones this falls in the evening or very early morning, and we want you to make that call with full information rather than discover it after an offer.
- Direct reports: None. This role has no one reporting into it. Your impact comes entirely through influence, documentation, and follow-through — not through managing people. However, admin and other support is available.
- Tools: Google Workspace, Slack, ClickUp, and our internal client-delivery platform. Training provided on our specific systems; prior experience with similar tools (Asana, Monday.com, Notion, Trello) is a strong substitute.
- Communication standard: Written updates are specific, dated, and attributed to a named owner. We don't use vague status language like "on track" or "in progress" — every report says what was done, by whom, with a result attached.
Send a video, a brief one, your resume, anything else we should know to [email protected], subject is "SUCCESS". We move fast.